An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

Sachin A. Sasane; Nandu B. Bhise; Girij P. Singh; Alex Joseph; Gautham G. Shenoy

doi:10.1080/00397911.2019.1622018

An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

Sachin A. Sasane^*
, Nandu B. Bhise
, Girij P. Singh
, Alex Joseph
, Gautham G. Shenoy

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9%, [α]_D²⁰ = +35.37° (c = 0.90, acetonitrile)) without use of preparative HPLC is described. This process involves effective purification of hydroxyl intermediate (5A) through solvent crystallization followed by inhibition of inversion of the chiral center at C-15 position. This was possible due to judicious use of diol intermediate (6) for double bond reduction prior to hydroxyl protection.

Original language	English
Pages (from-to)	2350-2356
Number of pages	7
Journal	Synthetic Communications
Volume	49
Issue number	18
DOIs	https://doi.org/10.1080/00397911.2019.1622018
Publication status	Published - 17-09-2019

All Science Journal Classification (ASJC) codes

Organic Chemistry

Access to Document

10.1080/00397911.2019.1622018

Cite this

@article{ad58951754f94b8b8aabee42d9df455b,

title = "An improved synthesis of latanoprost involving effective control on 15(S) diastereomer",

abstract = "An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9\%, [α]D20 = +35.37° (c = 0.90, acetonitrile)) without use of preparative HPLC is described. This process involves effective purification of hydroxyl intermediate (5A) through solvent crystallization followed by inhibition of inversion of the chiral center at C-15 position. This was possible due to judicious use of diol intermediate (6) for double bond reduction prior to hydroxyl protection.",

author = "Sasane, \{Sachin A.\} and Bhise, \{Nandu B.\} and Singh, \{Girij P.\} and Alex Joseph and Shenoy, \{Gautham G.\}",

note = "Publisher Copyright: {\textcopyright} 2019, {\textcopyright} 2019 Lupin Limited.",

year = "2019",

month = sep,

day = "17",

doi = "10.1080/00397911.2019.1622018",

language = "English",

volume = "49",

pages = "2350--2356",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "18",

}

TY - JOUR

T1 - An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

AU - Sasane, Sachin A.

AU - Bhise, Nandu B.

AU - Singh, Girij P.

AU - Joseph, Alex

AU - Shenoy, Gautham G.

PY - 2019/9/17

Y1 - 2019/9/17

N2 - An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9%, [α]D20 = +35.37° (c = 0.90, acetonitrile)) without use of preparative HPLC is described. This process involves effective purification of hydroxyl intermediate (5A) through solvent crystallization followed by inhibition of inversion of the chiral center at C-15 position. This was possible due to judicious use of diol intermediate (6) for double bond reduction prior to hydroxyl protection.

AB - An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9%, [α]D20 = +35.37° (c = 0.90, acetonitrile)) without use of preparative HPLC is described. This process involves effective purification of hydroxyl intermediate (5A) through solvent crystallization followed by inhibition of inversion of the chiral center at C-15 position. This was possible due to judicious use of diol intermediate (6) for double bond reduction prior to hydroxyl protection.

UR - https://www.scopus.com/pages/publications/85069525544

UR - https://www.scopus.com/pages/publications/85069525544#tab=citedBy

U2 - 10.1080/00397911.2019.1622018

DO - 10.1080/00397911.2019.1622018

M3 - Article

AN - SCOPUS:85069525544

SN - 0039-7911

VL - 49

SP - 2350

EP - 2356

JO - Synthetic Communications

JF - Synthetic Communications

IS - 18

ER -

An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this